methyl 5-N-acetylamino-2,6-anhydro-8-azido-3,4-di-O-benzyl-5,7,8-trideoxy-D-glycero-L-gluco-octuronate

Base Information

Chemical Name:methyl 5-N-acetylamino-2,6-anhydro-8-azido-3,4-di-O-benzyl-5,7,8-trideoxy-D-glycero-L-gluco-octuronate
CAS No.:537031-62-2
Molecular Formula:C₂₅H₃₀N₄O₆
Molecular Weight:482.536
Hs Code.:

Synonyms:methyl 5-N-acetylamino-2,6-anhydro-8-azido-3,4-di-O-benzyl-5,7,8-trideoxy-D-glycero-L-gluco-octuronate

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Chemical Property of methyl 5-N-acetylamino-2,6-anhydro-8-azido-3,4-di-O-benzyl-5,7,8-trideoxy-D-glycero-L-gluco-octuronate

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Technology Process of methyl 5-N-acetylamino-2,6-anhydro-8-azido-3,4-di-O-benzyl-5,7,8-trideoxy-D-glycero-L-gluco-octuronate

There total 8 articles about methyl 5-N-acetylamino-2,6-anhydro-8-azido-3,4-di-O-benzyl-5,7,8-trideoxy-D-glycero-L-gluco-octuronate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: (2S,3S,4R,5S,6R)-5-Acetylamino-3,4-bis-benzyloxy-6-(2-methanesulfonyloxy-ethyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

: 537031-62-2
methyl 5-N-acetylamino-2,6-anhydro-8-azido-3,4-di-O-benzyl-5,7,8-trideoxy-D-glycero-L-gluco-octuronate

Guidance literature:: With sodium azide; In N,N-dimethyl-formamide; at 90 ℃;
DOI:10.1016/S0008-6215(02)00487-1

Reference yield:

: 262286-48-6
3-(2'-N-acetylamino-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl)-1-propene

: 537031-62-2
methyl 5-N-acetylamino-2,6-anhydro-8-azido-3,4-di-O-benzyl-5,7,8-trideoxy-D-glycero-L-gluco-octuronate

Guidance literature:: Multi-step reaction with 8 steps

1: 91 percent / TMSOTf / CH₂Cl₂ / 1 h / -40 °C

2: 98 percent / NaOMe / methanol / 20 h / 20 °C

3: Jones reagent / acetone / 48 h / 20 °C

4: 62 mg / NaHCO₃ / dimethylformamide

5: OsO₄; NaIO₄ / tetrahydrofuran; H₂O / 20 h / 20 °C

6: 66 mg / NaBH₄ / methanol / 20 h / 20 °C

7: TEA / CH₂Cl₂ / 0 - 20 °C

8: NaN₃ / dimethylformamide / 90 °C

With sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; sodium azide; jones reagent; trimethylsilyl trifluoromethanesulfonate; TEA; sodium methylate; sodium hydrogencarbonate; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0008-6215(02)00487-1

Reference yield:

: (2S,3S,4R,5S,6R)-5-Acetylamino-3,4-bis-benzyloxy-6-(2-oxo-ethyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

: 537031-62-2
methyl 5-N-acetylamino-2,6-anhydro-8-azido-3,4-di-O-benzyl-5,7,8-trideoxy-D-glycero-L-gluco-octuronate

Guidance literature:: Multi-step reaction with 3 steps

1: 66 mg / NaBH₄ / methanol / 20 h / 20 °C

2: TEA / CH₂Cl₂ / 0 - 20 °C

3: NaN₃ / dimethylformamide / 90 °C

With sodium tetrahydroborate; sodium azide; TEA; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(02)00487-1